2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal

Base Information

• Chemical Name: 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal
• CAS No.: 93292-41-2
• Molecular Formula: C₂₈H₄₂O₃S₂Si
• Molecular Weight: 518.857
• Mol file: 93292-41-2.mol

Synonyms:2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal

Chemical Property of 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal

There total 6 articles about 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

(S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol (94292-91-8) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-Butyl-[(S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propoxy]-diphenyl-silane (85593-59-5,93292-41-2)

Guidance literature:

With triethylamine; dmap; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)99055-5

Reference yield:

D-Arabinose (10323-20-3) → 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal (93292-41-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / 6 M aq. HCl / 2.5 h

2: 92 percent / H₂SO₄ / 16 h / Ambient temperature

3: 64 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 1 h / 23 °C

4: 95 percent / LiAlH₄ / tetrahydrofuran / 3.5 h / Ambient temperature

5: 1.) NaHMDS / 1.) THF, -78 deg C, 0.5 h, 2.) THF, from -78 to 15 deg C, 22 h

With hydrogenchloride; lithium aluminium tetrahydride; sulfuric acid; potassium tert-butylate; sodium hexamethyldisilazane; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/ja00128a008

Reference yield:

2-deoxy-4,5-O-isopropylidene-D-erythro-pent-1-enose diethyl dithioacetal (64722-92-5) → 2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal (93292-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / LiAlH₄ / tetrahydrofuran / 3.5 h / Ambient temperature

2: 1.) NaHMDS / 1.) THF, -78 deg C, 0.5 h, 2.) THF, from -78 to 15 deg C, 22 h

With lithium aluminium tetrahydride; sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/ja00128a008

upstream raw materials:

(S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol

tert-butyldimethylsilyl chloride

1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol

2-deoxy-4,5-O-isopropylidene-D-erythro-pent-1-enose diethyl dithioacetal

Downstream raw materials:

(E)-(S)-5-(tert-Butyl-diphenyl-silanyloxy)-8-oxo-oct-6-enoic acid methyl ester

methyl 5(S)-(tert-butyldiphenylsilyl)oxy-6-oxo-hexanoate

C₃₅H₄₈O₅Si

C₃₂H₄₄O₅Si

Refernces

• 1、 Leblanc, Yves,Fitzsimmons, Brian,Adams, Julian,Rokach, Joshua. "TOTAL SYNTHESIS OF LIPOXIN B: ASSIGNMENT OF STEREOCHEMISTRY". . p. 1399 - 1402. Retrieved 2007/10/02.